(3E,2R,6R,8S)-1-benzyloxy-2,4,8-trimethylundec-3-en-6-ol | 1361023-02-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3E,2R,6R,8S)-1-benzyloxy-2,4,8-trimethylundec-3-en-6-ol
• 英文别名: (2R,6R,8S,3E)-1-benzyloxy-2,4,8-trimethylundec-3-en-6-ol；(E,2R,6R,8S)-2,4,8-trimethyl-1-phenylmethoxyundec-3-en-6-ol
• CAS: 1361023-02-0
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: IODQZDPOXPLFHV-GTUUOVHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(-)-β-香茅醇 在 咪唑 、 盐酸 、 bismuth(III) iodide 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 臭氧 、 三苯基膦 、 diisopropyl azodicarboxylate 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 77.5h， 生成 (3E,2R,6R,8S)-1-benzyloxy-2,4,8-trimethylundec-3-en-6-ol
  参考文献：
  名称：

  Systematic Comparison of Sets of ¹³C NMR Spectra That Are Potentially Identical. Confirmation of the Configuration of a Cuticular Hydrocarbon from the Cane Beetle Antitrogus parvulus

  摘要：

  A systematic process is introduced to compare (13)C NMR spectra of two (or more) candidate samples of known structure to a natural product sample of unknown structure. The process is designed for the case where the spectra involved can reasonably be expected to be very similar, perhaps even identical. It is first validated by using published (13)C NMR data sets for the natural product 4,6,8,10,16,18-hexamethyldocosane. Then the stereoselective total syntheses of two candidate isomers of the related 4,6,8,10,16-pentamethyldocosane natural product are described, and the process is applied to confidently assign the configuration of the natural product as (4S,6R,8R,10S,16S). This is accomplished even though the chemical shift differences between this isomer and its (16R)-epimer are only ±5-10 ppb (±0.005-0.01 ppm).

  DOI：

  10.1021/jo5012027

文献信息

• Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry
  作者：Norazah B. Basar、Hao Liu、Devendra Negi、Hasnah M. Sirat、Gareth A. Morris、Eric J. Thomas

  DOI：10.1039/c2ob06906g

  日期：——

  The stereoselective reaction of an allyl bromide with an aldehyde mediated by a low valency bismuth species was the key reaction in stereoselective syntheses of (4S,6R,8R,10S,16S)- and (4S,6R,8R,10S,16R)-4,6,8,10,16-pentamethyldocosanes. 13C NMR data for these compounds confirmed that the cuticular hydrocarbon isolated from the cane beetle Antitrogus parvulus was the (4S,6R,8R,10S,16S)-stereoisomer.

  在低价铋物种介导下，烯丙基溴与醛的立体选择性反应是合成(4S,6R,8R,10S,16S)-和(4S,6R,8R,10S,16R)-4,6,8,10,16-五甲基二十二烷的关键反应。这些化合物的13C核磁共振数据证实，从甘蔗甲虫Antitrogus parvulus分离得到的蜡质烃为(4S,6R,8R,10S,16S)-立体异构体。
• Systematic Comparison of Sets of ¹³C NMR Spectra That Are Potentially Identical. Confirmation of the Configuration of a Cuticular Hydrocarbon from the Cane Beetle <i>Antitrogus parvulus</i>
  作者：Norazah Basar、Krishnan Damodaran、Hao Liu、Gareth A. Morris、Hasnah M. Sirat、Eric J. Thomas、Dennis P. Curran

  DOI：10.1021/jo5012027

  日期：2014.8.15

  A systematic process is introduced to compare (13)C NMR spectra of two (or more) candidate samples of known structure to a natural product sample of unknown structure. The process is designed for the case where the spectra involved can reasonably be expected to be very similar, perhaps even identical. It is first validated by using published (13)C NMR data sets for the natural product 4,6,8,10,16,18-hexamethyldocosane. Then the stereoselective total syntheses of two candidate isomers of the related 4,6,8,10,16-pentamethyldocosane natural product are described, and the process is applied to confidently assign the configuration of the natural product as (4S,6R,8R,10S,16S). This is accomplished even though the chemical shift differences between this isomer and its (16R)-epimer are only ±5-10 ppb (±0.005-0.01 ppm).